


Lily's First Day

by ChibiCream (ChibiDream)



Category: Original Work
Genre: Blow Jobs, Bribery, College Student, Come Swallowing, Embarrassment, F/M, First Time, First Time Blow Jobs, Forehead Kisses, Gentle Kissing, Harems, Hugs, Kissing, Light Dom/sub, Manipulation, My First Smut, Naked Cuddling, Nervousness, Stripping, Teasing
Language: English
Status: Completed
Published: 2021-01-31
Updated: 2021-01-31
Packaged: 2021-03-17 09:15:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,714
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29097894
Author URL: https://archiveofourown.org/users/ChibiDream/pseuds/ChibiCream
Summary: After being unable to pay for her upcoming monthly university tuition, Lily is given an offer from a school friend to help her out of her financial situation. However, when the time arrives to complete her end of the deal, she starts to have second thoughts, forcing Yuki to convince her to follow through.(Might turn this into a collection of short stories in the future. For now, it's on its own though.)
Kudos: 4





	Lily's First Day

Joining a harem was certainly not on the list of paths Lily believed she would take in her lifetime, nor was it a particularly appealing one either. "Leading Neurological Scientist and Psychologist" is a better title to behold than "Member of Large Harem", and the latter isn't exactly something one would be proud to write to their parents about. Nevertheless, Yuki was on his way over to her house to induct her into the group and to make her officially work under his _leadership,_ whatever leadership meant in this scenario. The relationship was less one of authority and more one of mutual agreement, a deal for security and pleasure on both sides. Everyone got what they wanted, in the end. Yuki used his harem to sate his sexual or emotional desires, and in return, each member received their material, monetary, or emotional requests in turn. More personal of a relationship than prostitution, but less binding than a sugar daddy. A necessary balance for Lily to have considered, let alone accepted, the proposition. Perhaps, however, she jumped at the chance too willingly. Even with tuition for college weighing on her mind, there were more ethical but, albeit, energy induced ways of earning money. Then again, it wasn't the paycheck that brought her to accept the offer.

She was laying in her bed, staring up at the white ceiling with thoughts floating around on the paint surface. Scrambling to pay off the previous year of university was a nightmare, one she didn't want to repeat again in the upcoming months, but was this the way to do it? It wasn't a mistrust of Yuki that was the problem. He definitely had the money since he was born into a rich family, though not everyone knew this. She could only recall a few people at her school who knew of his status. No, the issue had more to do with the concept. Sure, it was easier to see past, having known him for so long, but it also seemed unhealthy to shift a relationship in this drastic of a redirection. Then there was the point of her inexperience and her anxiety in unfamiliar situations.

That was it, she was calling it off.

She grabbed her phone off the nightstand and sat at the edge of her bed, chin resting on one of her knees while the other leg dangled off the bed. The phone rested against her ear as the phone rang, waiting for Yuki to pick up. Yet, after a few seconds of letting it ring, she hung up before he could answer. She couldn't let her nervous wreck of a mind get in the way like it always does, especially not after assuring him so many times that she was wanting to go through with it. Her emotions were just getting the better of her. Once he got here she'd be alright, she thought. It was like stage fright. That's why she made sure her parents would be far away out of town before attempting something like this. The fear of being caught would only add to the already unnecessarily high amounts of stress she was feeling.

Figuring out what to wear attributed to the spikes in anxiety. Not being told what to put on or what they would even be doing made outfits difficult to decide. He probably wouldn't mind her usual style, so she wore a pastel blue hoody and jeans with some black socks with hot pink diamonds on them for flare. A basic set but one she enjoyed nonetheless. It may not be harem worthy. So be it. If anything it was his fault for only saying he'd show up at her house without giving her any instructions. Other than her clothes, she went as far as to brush her hair to make it presentable and didn't bother with makeup, her hand probably wouldn't stay steady if she tried to apply some. Surely he wouldn't expect anything exceptional out of a new person.

Finally, after a while longer of waiting, she heard a knock on the door downstairs and got up to go answer it. Sure enough, it was Yuki, luckily standing there in his own jeans and hoodie which gave her a small sense of relief, a relief that went away as quickly as it came.

"Hello Lily, I hope you're doing well today," he said in his usual calming tone. Having gone through the same first-day experience with many other people, it was natural to assume hesitant responses upon his arrival. Admittedly, not everyone was reserved to the idea, but the majority started off in that state.

"It's been rather uneventful so far," she replied, hand still gripping rather tightly on the doorknob. "My parents left this morning and won't be back for a few days."

"What did you have to do to make that happen?" He asked with a small smile.

"Nothing, they were leaving either way." She stood in the doorway for a while in silence, sometimes glancing down at his hands which were in the pockets of his hoodies. After a couple minutes, she finally asked, "Would you like to come inside?" He nodded and went in.

"You do remember why I am here, yes?"

The question didn't come across as patronizing, moreso curious. "To be honest, I'm not entirely sure. You haven't told me what we're doing and I've been lost in my own head because of it."

"Well, are you aware of what a harem is?"

"Yes, I'm not that stupid. Isn't there like a list of prerequisites we need to finish first?"

"Most people go on a date first, but we're skipping that part. The only real step we need to do is get you out of this," he said, pinching at her hoodie and pulling on it.

She shied away at the remark, looking off to the side at anything other than him. "How can you be so calm about this?"

"I've done it a few times before, and besides, if I was freaking out that probably wouldn't put you at ease."

"I was actually about to call you to tell you I changed my mind, but I think it's just me worrying as usual."

"There's still time to back out. I haven't transferred anything to your account yet," he replied, letting go of her hoodie and returning his hand to his pocket.

"When will you do that?"

"Whenever we start, assuming we do at all. It's still your choice. I will say that most people are put off at first, but it gets easier over time."

"I'm just worried. Not entirely sure why. Too good to be true, maybe?"

"The offer can change if that will make your first experience in the harem easier for you. I'll only give you half this week's tuition, but we won't go too far with it. That means that even if you get the full amount in the next three weeks, you'd have to come up with an eighth of next month's payment. Then again, you'd have a bit more time to adjust and gauge your willingness for next week."

She still refused to look at him as she considered the idea, staring at the television in the living room that was looking back at her with a black screen. "How far is not too far?"

"Depends, how far is it for you? I'm willing to let you strip down with letting me touch you, or I can feel you around without taking anything off."

"I think I'd prefer that first one. I've been mentally preparing myself to have to do that anyway."

"Would you like to go up to your room then?" He asked, pulling out his phone getting ready to move over the money to her.

"Yeah, I guess so."

They both started up the stairs, Yuki still looking at his phone as he climbed and setting the numbers to half their original values. Part of him was a little annoyed to have her back out slightly, but it was to be expected. When they entered the room he finished up sending the money, sat down on the bed, and put the phone face down under it, making sure Lily saw him do it.

"No chance for photos. There won't be anything blackmailing you to stay in the harem, okay?"

She nodded, watching the floor and standing rather close to her bedroom door. It remained quiet for a few minutes since Yuki didn't want to overwhelm her, however, not that his end of the deal was complete, he wasn't leaving without seeing her more... appealing side. "You don't need to wait for me to tell you to, you can take things off whenever you're ready," he prodded her with no response. Another few minutes passed with no change. "I suppose acting on your own would be difficult for your first go-round. In that case..." He curled his finger toward himself, beckoning her to come stand in front of him which she did, making her way over slowly and hesitantly.

"You said you'd be more comfortable taking it off for me. What's the matter?"

The hoodie was being tugged on again and she felt the pulling get a bit stronger as if he was trying to draw her closer. "Kind of distracted, I guess."

"Purposefully?" She shrugged at him. "I would call it off but I ran the transfer a little too soon."

"I can send it back to you if you want."

"Well, what I want is for you to do what I came here for. That doesn't seem like it's going to happen though."

"My body is tensing up on its own. There's nothing I can do about it. Sorry."

"There was another option if you're willing to sit next to me and hold still a bit."

"You could just leave me the money and go home you know," she said half-joking and half hoping. Then he patted the mattress next to him and she knew that hope wasn't happening.

The moment she sat next to him he wrapped one arm around her side in a half embrace, both to calm her and to keep her steady. They were shoulder to shoulder, and she was inclined to lean her head on him but thought better of it. Instead, she watched his other hand reach between her hoodie and t-shirt, rubbing his hand along her stomach through the fabric. Feeling a guy's touch under these circumstances did not help her need to grip onto the blanket nervously. Most of her weight had shifted onto her hand, the only thing other than his arm keeping her from falling over onto her side, or jumping away from him for that matter.

Once he was sure her initial reactions of shock were dissipating, he moved his hand under her shirt for the first bit of skin-to-skin contact she's had under his watch. He wrapped around to the other side of her body and pulled the arm on her shoulder down to meet the other, completing the embrace around her stomach which lifted her shirt up slightly above her waistline. Honestly, if this was all there was, she wouldn't mind the situation.

Her body was pulled back closer to him as he placed his chin on her shoulder, lightly whispering into her ear, "You're really warm. It's rather comforting. I kind of want to go to sleep like this."

"Umm... what?" She exclaimed, caught off guard a bit.

"Your parents won't be back today you said. Take off your top. I'll stay the night and leave in the morning."

"O-Okay... If that's what you want."

He let go of her and laid back until he was laying on the bed with his legs hanging off, of course, not letting her off without watching her from behind. It was the slowest he had ever seen a girl take off anything, the edge of the shirt inching its way up her back and freezing for a minute when it reached the chest line. He knew why too. Feeling down her back a bit ago, he realized there wasn't a bra underneath.

Before raising her clothes any further, she looked back to see that he was indeed staring at her, somewhat absentmindedly as he noted her pleasant milky white skin and pink expression embedded in her face. She turned back to look at her wall and, with a couple deep breaths, bit her lip and brought everything off the rest of the way and threw it beside her onto the bed. Then, without giving her any time to adjust, Yuki lunged at her, hugged her from behind just under her chest, and crashed her down onto the pillows. She let out a small "eep" out of surprise and her head hit the mattress while the boy moved his legs to more affectively spoon her.

Her pants were getting in the way of him fully enjoying lying next to her, so in an attempt to remedy that, he muttered, "If it'd be more comfortable for you, you can take off your jeans. I doubt you sleep like this."

"I don't think I could sleep even if I did..." There was a small nudging of his finger around her waistline. "Is this what the harem is like? You poking and pulling until you get what you want."

"Partially. I'm nothing if not persistent."

"Annoying is more like it."

"While I'll always be determined to get the outcome I desire out of you, it won't be out of force. I have no intentions of making you do anything against your will. It's always your choice in the end."

"Then why are you being so pushy?" She asked a bit more irritated.

"It's a harem, that's part of my job," he answered nonchalantly.

"No, really, why? You don't normally act like this."

"I simply like getting what I want, do I need more motivation than that? If I'm going to be shelling out so much money to a large number of people then I'd like to get paid back. There's no reason for me to hand out loans, I have no interest in wealth, my parents have ruined that for me. Plus, it doesn't truly change your financial situation. So, the game is I help you out, and you let me have some fun, simple as that. Which means when I grab a four-hour flight in the hopes of gaining a new member after asking hundreds of times if they're sure they're willing to do it, forgive me for getting a little peeved when they seem less than responsive."

She sat up and glared at him, being sure to cross her arms over her chest. "Yes, I said I'd do it, but you never even told me what joining would entail. I'm sorry that I don't meet your unspoken qualifications. Besides, saying that over the phone is different when you're hundreds of miles away. Now that you're here in my bedroom..." This was cut off by Yuki reaching under the bed to grab his phone as if he wasn't listening. Her hands balled into fists as mere irritation turned to pissed until he looked up at her as her phone buzzed in her pocket. She took it out and looked at the message sent from him, reading through it and then setting her phone down on the bed.

"That's everything I want to do over the next eight to ten hours. Nothing more nothing less. That's for the full amount for the week instead of only half. It's not the list I had in mind when I flew in, but it's the one I have now. Take it or send back the first part of my transfer by tomorrow morning. Is that more clear?"

"Yes..." She said, her anger interrupted by the new terms.

"It's a harem. I'm not sure what else you expected."

"Everything here, and that's it?" She was reading through the list over and over to make sure she wasn't missing anything.

"Exactly as stated."

Biting her lip, she pondered again, this time weighing her options without the nervous wreck side of her mind impeding. "I can't believe I'm considering this for tuition money..."

"You're high if you think I'm giving anything for nothing."

"This is really pushing your luck."

"You pushed first."

"Fine, okay. I'll do it." The words barely escaped her mouth before she felt him wrapping his arms around her stomach again, his head burying itself into her neck. "Stop being so eager, you're going to make me freeze up again."

"Stop leaving me waiting then," was all he said before kissing Lily's neck and grabbing onto her tighter. He switched between her neck and her cheek at random, pressing his lips into both. The warmth of her skin was leaking into his hoodie along with the strawberry scent of her shampoo. "Kiss me back why don't you?"

"That wasn't on your list," she said flatly.

"Then quit stalling." His hand moved from her stomach to run it up and down her denim-covered thigh.

"Let go so I can stand at least." He obliged and loosened his hold, allowing her to slide off the bed with her back facing him again. A part of him wanted to make her turn around, but he kept it to himself as she unbuttoned her jeans and slowly got them off in small increments, needing to fight against the skin-tight pants gripping onto her. Once she was able to kick them off, she repeated the process more quickly with her white panties, taking them off as well while a huge wave of vulnerability washed over her. She stood back up, but froze up the moment she did, staring off at a blank spot on her wall.

"Lily, you're spacing out again. Let me see my new harem girl." With those words she turned around, arms behind her as hiding wouldn't do her anymore good, however, she couldn't help crossing her legs a little. She didn't look him in the eyes, turning her head to the side to show that her cheeks were flushed, a sight that made Yuki smile to himself. "You know, you're really cute when you're nervous."

She ignored his compliment. "Can we just get this over with?"

"If you'd prefer, but you're being no fun," he said, sitting up and scooting over to the edge of the bed in front of her. While she was taking off her jeans, Yuki was taking off his own, leaving nothing covering him from the waist downward. The sight did not help her current state of paralysis. "Learn to enjoy it. Everything goes by a lot faster if you do. Now, get on your knees," he demanded, moving his legs to hang off the side of the mattress and spreading them apart a tad.

Against instincts, she lowered herself onto her knees and positioned her face between his legs, noting his size was larger than she expected which made her weary. It seemed to reach up toward her mouth as if it had its own mind, like it already knew what she needed to do. "Just this and napping for a while, then you'll leave, right?"

"Yup, the quicker you start the less you have to sit there worrying," he replied, toying with her hair by twisting it around his fingers.

She took the advice and licked him once to ease herself into what this was going to be like. "Why does it taste salty?"

"Come on Lily, are you distracting yourself on purpose?"

"No, my head goes random places on its own. It's a genuine question though."

"If you weren't completely new to this I'd think you were teasing me. That's just how it tastes, not much more of an explanation for it."

"I see." There was a pause and then she asked, "How many times do I have to make you... you know..."

"Once. At the rate you're going, we'll be here all day."

Her eyes rolled. "Is this what you want?" She asked, her tone heated, as she opened her mouth and shoved her face down onto his dick about four inches before recoiling as she coughed up any fleeting confidence she had in the moment.

All Yuki could do was laugh as his fingers traversed her long flowing locks, ending with his hand lightly cupping her cheek. "No, choking yourself doesn't get either of us anywhere."

"It looks so easy when others do it..."

"Your gag reflex doesn't go away on its own. You have to practice to get to that point."

"Well I'm sure as hell not practicing for you."

"Maybe not, but you're not doing any of this for me to begin with. Quit getting sidetracked or I'll go back to only giving you half the tuition," he ordered, moving his cock so that it rested against her lips.

In order to respond, she moved her head back. "You can't change the deal whenever you want!"

"My end of the deal is done. You're the one who won't do yours. So, one more distraction and I'm leaving you with only half of it transferred."

She wanted to respond, but his eyes told her he wasn't joking. With a small gulp to clear her throat of more arguments, she moved her head back to where her lips brushed up against the end of his dick and licked it cautiously. The bitter salty taste was spread across her tongue as she pressed herself against him, feeling how hot his bare skin was against her. Her face was red with embarrassment, every movement of her tongue feeling weirder than the last. One moment she was transfixed on the taste in order to avoid the actions from taking over her consciousness. Others she was focussed on her touch to try and get this over with as quickly as possible. Her mind switched between these states, unable to empty her thoughts.

"You're really cute you know. Even if your personality is like an ignorant brat."

"Shut up! I'm figuring it out."

"Scratch that, your attitude is cute too."

"Quit distracting me why don't you," she said, stopping to glare at him.

"Not one for compliments then? If we're going to take a nap after this you should lighten up a little."

"If that's your attempt at this whole calming me down thing, you're not very good at."

"Not part of the agreement. You can't go changing it whenever you want." 

There was a small glare from her after hearing him use her words to his advantage. She went back to the struggling attempt at a blowjob, using what little knowledge she had from friends' stories and unrelated books. Then again, it was doubtful that many would have advice for this type of situation. Other than her hair, he didn't move to touch anything else, preferring to play with it the same way he does his own when he's fidgeting, weaving the strands around his fingers.

Soon she moved from only using her tongue to her mouth, letting an inch or so inside her for the first, and hopefully only, time. He made no obvious reactions to this, choosing not to interrupt her, but she did feel one of his hands move to her cheek, lightly cupping it in some affectionate gesture. Her head bobbed back and forth along his dick, not moving much, but getting a better feel for her own actions. Slowly she felt comfortable with trying to push onto him more. He was careful not to surprise her with any sudden motions, allowing him to soak in the pleasure of her mouth around him. At times he couldn't tell if her cheeks were warmer than the back of her throat, but her inability to keep her face from heating up was in itself arousing.

"Go a bit faster," he requested, and despite a part of her wanting to bite down on him, she did as he asked, scooting forward slightly to allow herself more room to work. For several minutes, he felt her gradually increase in speed and improve her rhythm greatly from when she started. Her breathing was one of the few noises resonating in the room and was only now following in beat with when she pulled back from his dick. It seemed university students were fast learners after all.

It wasn't too much longer before he felt close to climax, a feeling he wished he was sharing with her. Nevertheless, in a low whisper, he said, "I'm about the cum Lily. You're doing a great job," while caressing her cheek with the back of his fingers. Only a fool would move to shatter the fragile sense of security that had been built, but he couldn't help entertaining the thought of pulling on her hair a bit, if only in a teasing gesture. Her mouth continued to run along his dick. After hearing his words, she partially closed her eyes, somewhat expecting him to finish mere seconds after he said he was going to. She had no idea it was happening until he leaned forward and grabbed the back of her head, forcing her to stop just as her lips were near the tip of his cock. Her eyes looked up at him somewhat pleadingly, but it was difficult to tell what she was pleading for. He held her there as he came, releasing his hot sperm all over her tongue and making her taste his seed for the first time. There was a slight wince of surprise in her face as the first white strands shot into her mouth. It was salty and bitter, but certainly not the worst thing she'd tasted. How sticky and slimy it was threw her off the most, especially as she was made to swallow it all down bits at a time. When he was finished, he let go of her and asked her to open her mouth. She did so hesitantly, showing she had drunk everything properly.

"You were getting pretty good at it by the end Lily," he said, lowering himself to the floor in front of her and kissing her on the forehead. "Thought you said you weren't going to practice for me."

"Just send me the rest of the money why don't you."

He nodded and pulled out his phone, sending the transfer request quickly and then immediately kissing her again on the cheek. "Feel free to come back to me if you ever need more."

"Don't count on it," she muttered as he embraced her again, reminding her he still wanted to lay in bed with her for the afternoon. At least that wouldn't be as bad, even with the taste of his sperm still lingering in her mouth.

When he asked her to do so, Lily climbed into the bed and lied on her side, allowing him to wrap his arms around her from behind. This time, he intentionally held her around her chest, squeezing her lightly and feeling the soft squish of her breasts against him. At first, there was no doubt in her mind that she wouldn't be able to sleep, but when he buried his face in her hair and started dozing off himself, she couldn't help feeling calmed by the steady rhythm of his breathing. However, it didn't take long for the cold air of the outside to creep into the room. Since he didn't pull the blanket over them before falling asleep, she had to press her body closer to him to keep a comfortable temperature, something she was sure he was enjoying even in his sleep. Even so, she eventually closed her eyes with a small thought tempting her in the back of her mind. _Maybe I could do this more often._

* * *

It's my first time attempting something in the realm of explicit content, so I hope you enjoyed the story! If you did, you can follow my twitter for updates on fanfictions that I'm writing. I post updates to current works, notify followers of new works, and outside of fanfiction I also write original fiction as well. I am fine with people tweeting requests for stories or ships at me, just know I might not get to it.

[@ChibiDreamWrite](https://twitter.com/ChibiDreamWrite)


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